Furofuranonaphthoquinones: bioactive compounds with a novel fused ring system from crescentia cujete

Carl E. Heltzel, Leslie Gunatilaka, T. E. Glass, David G I Kingston

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Bioassay-directed fractionation of the methyl ethyl ketone extract of Crescentia cujete yielded the naphthoquinones 1 and 2. Both compounds are cytotoxic, and 1 shows selective DNA-damaging activity against yeast. Detailed spectroscopic interpretation led to the assignment of the structures of 1 and 2 as 3-hydroxymethylfuro[3,2-b]naphtho[2,3-d]furan-5,10-dione and 9-hydroxy-3-hydroxymethylfuro[3,2-b]naphtho[2,3-d]furan-5,10-dione, respectively. This is the first report of this fused furofuran ring system, either as a natural product or a synthetic substance.

Original languageEnglish (US)
Pages (from-to)6757-6762
Number of pages6
JournalTetrahedron
Volume49
Issue number31
DOIs
StatePublished - Jul 30 1993
Externally publishedYes

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Naphthoquinones
Bioassay
Fractionation
Biological Products
Biological Assay
Yeast
Yeasts
DNA
furan
methylethyl ketone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Furofuranonaphthoquinones : bioactive compounds with a novel fused ring system from crescentia cujete. / Heltzel, Carl E.; Gunatilaka, Leslie; Glass, T. E.; Kingston, David G I.

In: Tetrahedron, Vol. 49, No. 31, 30.07.1993, p. 6757-6762.

Research output: Contribution to journalArticle

Heltzel, Carl E. ; Gunatilaka, Leslie ; Glass, T. E. ; Kingston, David G I. / Furofuranonaphthoquinones : bioactive compounds with a novel fused ring system from crescentia cujete. In: Tetrahedron. 1993 ; Vol. 49, No. 31. pp. 6757-6762.
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